US4536509A - 1,1-Diaryl-2-azolylethanes and preparations containing these compounds - Google Patents

1,1-Diaryl-2-azolylethanes and preparations containing these compounds Download PDF

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US4536509A
US4536509A US06/585,621 US58562184A US4536509A US 4536509 A US4536509 A US 4536509A US 58562184 A US58562184 A US 58562184A US 4536509 A US4536509 A US 4536509A
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sub
compound
compounds
active compound
plants
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Ulrich Hertenstein
Hilmar Mildenberger
Burkhard Sachse
Peter Hartz
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Hoechst AG
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Hoechst AG
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Assigned to HOECHST AKTIENESELLSCHAFT reassignment HOECHST AKTIENESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HARTZ, PETER, MILDENBERGER, HILMAR, SACHSE, BURKHARD, HERTENSTEIN, ULRICH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the invention relates to new 1,1-diaryl-2-azolylethyl derivatives, a process for the preparation of this substance class, and their use as biocides, in particular as fungicides.
  • the invention therefore relates to new 1,1-diaryl-2-azolylethanes of the general formula (I) ##STR2## in which Ar 1 and Ar 2 represent identical or different radicals which have the meaning of naphth-1-yl or naphth-2-yl, tetrahydronaphth-1-yl or tetrahydronaphth-2-yl, indan-5-yl, five-membered or six-membered or benzo-fused five-membered or six-membered heterocyclic rings having up to two hetero-atoms which can be N, O or S, or in particular have the meaning of radicals of the formula (II) ##STR3## and in this formula, R 1 to R 5 are identical or different and preferably represent hydrogen, halogen, CF 3 , C 1 - to C 8 -alkyl, C 2 - to C 8 -alkenyl, C 5 - or C 6 -cycloalkyl, C 1 - to C 6
  • Z is a radical of the formula (III) ##STR4## in which R 6 denotes hydrogen or an alkyl or alkenyl radical which has up to 8, preferably 1 or 2, C atoms and which can be substituted by up to two alkoxy or amino groups which have 1 or 2 C atoms and which may also be different, but in particular is H, methyl or ethyl.
  • Az particularly represents 1,2,4-triazol-1-yl or 1,2,4-triazol-4-yl, or can also be benzimidazol-1-yl or pyrazol-1-yl.
  • the salts, complex salts and quaternization products of 1,1-diaryl-2-azolylethanes are also included.
  • the new compounds are obtained from compounds which carry an alcoholic OH group and are of the formula ##STR5## in which Ar 1 , R 6 and Az have the meanings given above, by reaction with aryl hydrocarbons of the formula (VI)
  • Ar 2 is one of the radicals given above.
  • the reaction is carried out in the temperature range from -15° to +150° C., preferably from -10° to 110° C., in the presence of an acidic catalyst, if appropriate in the presence of a diluent.
  • acidic catalysts are understood as meaning the conventional Friedel-Crafts catalysts, as described--like the suitable diluents--for example in Houben-Weyl, Methoden der org. Chemie, Vol. 7/2a, pages 17 to 21. Tetrachloroethane and aluminum trichloride are preferred. 1.1 to 2.5 equivalents of the catalyst and at least one equivalent of the aryl hydrocarbon H--Ar 2 , relative to the compound of the formula (V), are employed.
  • Examples of starting compounds of the formula (V) which are suitable for the preparation of the 1,1-diaryl-2-azolylethanes are: 1-(2,4-dichlorophenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)-ethane, 1-(2,4-dichlorophenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)-propane, 1-(2,4-dichlorophenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)-hexane, 1-(2,4-dichlorophenyl)-1-hydroxy-2-(1,2,4-triazol-1-yl)-octane, 1-(2,4-dichlorophenyl)-1-hydroxy-2-(imidazolyl-1-yl)-ethane, 1-(2,4-dichlorophenyl)-1-hydroxy-2-(imidazolyl-1-yl)-propane, 1-(2,4
  • aromatics of the formula H--Ar 2 (VI) are understood as meaning, for example: chlorobenzene, bromobenzene, 1,3-dichlorobenzene, 1,2-dichlorobenzene, 1,4-dichlorobenzene, toluene, xylene, mesitylene, 3-chlorotoluene, 4-chlorotoluene, anisole, pyridine, thiophene, benzothiophene, benzoxazole, benzthiazole, naphthalene, tetrahydronaphthalene and indane.
  • the procedure is carried out, in particular, as follows: the compounds of the formula (V), the aryl hydrocarbon H--Ar 2 (VI) and, if appropriate, a diluent are initially introduced, and the catalyst is slowly metered in at approx. -10° C. The mixture is allowed to reach room temperature in the course of 30 minutes, and is then heated until the evolution of gas begins. When this has ended, the mixture is heated for a further 30 minutes, allowed to cool to room temperature, poured onto ice, and rendered strongly alkaline with 50% strength NaOH, while cooling with ice, and the organic phase is then worked up in the conventional manner.
  • the 1,1-diaryl-2-azolylethanes according to the invention can occur in the E form and Z form.
  • they are furthermore capable of forming salts, complex salts and quaternization products.
  • Salts of organic and inorganic acids may be mentioned, such as, for example, acetates, fumarates, oxalates, benzoates, nitrates, bromides, chlorides and sulfates, salts of naphthalenesulfonic acids, complexes with metals of group 1b, 2b, 4b or 8b of the periodic table, for example copper, zinc and tin, and quaternization products with alkyl halides and phenacyl halides.
  • the preparation of such compounds is effected according to generally customary methods.
  • the compounds according to the invention, of the formula I are distinguished by an outstanding fungicidal action, in particular, for example, when used in plant protection.
  • fungal pathogens which have already penetrated the plant tissue can be successfully controlled by curative measures. This is particularly important and advantageous in the case of those fungal diseases which, after infection has occurred, can no longer be effectively controlled with the fungicides otherwise customarily used.
  • the spectrum of action of the claimed compounds includes, for example, in addition to various rust species, Phytophthora infestans, Plasmopara viticola and Piricularia oryzae, but in particular powdery mildew fungi in the cultivation of fruit, vegetables, cereal and decorative plants.
  • the excellent action of the compounds against powdery mildew species which are resistant to benzimidazole derivatives should be particularly singled out.
  • the substances are suitable for use in industrial fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling oils and cutting oils.
  • the agents can be used as wettable powders, emulsifiable concentrates, atomizable solutions, dusting agents, dressing agents, dispersions, granules or microgranules, in the conventional preparations.
  • Wettable powders are understood as meaning preparations which are uniformly dispersible in water and which also contain, in addition to the active compound and in addition to any diluent or inert substance, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl sulfonates or alkylphenyl sulfonates, and dispersants, for example sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or even sodium oleolylmethyl taurate.
  • wetting agents for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl sulfonates or alkylphenyl sulfonates
  • dispersants for example sodium ligninsulfonate, sodium 2,2'-dinaphthyl
  • Emulsifiable concentrates can be prepared, for example, by dissolving the active compound in an inert organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even high-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers.
  • an inert organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even high-boiling aromatics or hydrocarbons.
  • the solvent constituent can also be either completely or partially dispensed with.
  • emulsifiers which can be used are: calcium salts of alkylarylsulfonic acid, such as Ca dodecylbenzenesulfonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, fatty alcohol/propylene oxide/ethylene oxide condensation products, alkyl polyglycol ethers, sorbitane fatty acid esters, polyoxyethylene sorbitane fatty acid esters or polyoxyethylene sorbitol esters.
  • alkylarylsulfonic acid such as Ca dodecylbenzenesulfonate
  • non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, fatty alcohol/propylene oxide/
  • Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite or pyrophillite, or diatomaceous earth.
  • finely divided solid substances for example talc, natural clays, such as kaolin, bentonite or pyrophillite, or diatomaceous earth.
  • Granules can be prepared either by spraying the active compound onto absorptive, granulated inert material, or by applying active compound concentrations onto the surface of carriers, such as sand or kaolinites, or of granulated inert material by means of binders, for example polyvinyl alcohol, sodium polyacrylic or even mineral oils. It is also possible to granulate suitable active compounds in the manner customary for the preparation of fertilizer granules--if desired as a mixture with fertilizers.
  • carriers such as sand or kaolinites
  • binders for example polyvinyl alcohol, sodium polyacrylic or even mineral oils.
  • the active compound concentration is, for example, about 10 to 90% by weight, and the residual amount up to 100% by weight comprises conventional formulation constituents.
  • the active compound concentration can be about 10 to 80% by weight.
  • Dust-like formulations contain at most 5 to 20% by weight of active compound, and atomizable solutions contain about 1 to 20% by weight.
  • the active compound content depends in part on whether the active compound is present in liquid or solid form, and which granulation auxiliaries, fillers, etc. are used.
  • the active compound formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, solvents, fillers or carriers customarily used in the particular case.
  • the concentrates present in the commercial form are diluted in the conventional manner if appropriate, for example in the case of wettable powders, emulsifiable concentrates and dispersions, and also in the case of some of the microgranules, by means of water. Dust-like and granulated preparations, and atomizable solutions, are customarily no longer diluted with further inert substances before use.
  • a dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as the inert substance, and comminuting the mixture in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 64 parts by weight of kaolin-containing quartz as the inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyl taurate as the wetting agent and dispersant, and grinding the mixture in a pinned disk mill.
  • a dispersion concentrate which is readily dispersible in water is prepared by mixing 20 parts by weight of active compound with 6 parts by weight of alkylphenol polyglycol ether (Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 ethylene oxide units) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, approx. 255° to above 377° C.), and grinding the mixture in an attrition ball mill to a fineness of less than 5 microns.
  • alkylphenol polyglycol ether Triton X 207
  • isotridecanol polyglycol ether 8 ethylene oxide units
  • paraffinic mineral oil oil
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as the solvent and 10 parts by weight of oxyethylated nonylphenol (10 ethylene oxide units) as the emulsifier.
  • Wheat plants were treated, until dripping wet, with the compounds mentioned in Table III, amounts of 500, 250, 120 and 60 mg/liter of spray liquor being used. After the coating of active compound had dried off, the plants were strongly inoculated with spores of wheat brown rust (Puccinia triticina), and were placed for 24 hours in a climatically controlled chamber at 20° C. and 100% relative atmospheric humidity. Thereafter, the plants were placed in a greenhouse and were examined here, 14 days after inoculation, for infection with wheat brown rust. D served as the comparative agent.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Liquid Crystal Substances (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Steroid Compounds (AREA)
US06/585,621 1981-06-01 1984-03-07 1,1-Diaryl-2-azolylethanes and preparations containing these compounds Expired - Fee Related US4536509A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813121676 DE3121676A1 (de) 1981-06-01 1981-06-01 "1,1-diaryl-2-azolyl-aethane, ihre herstellung, ihre verwendung und diese verbindungen enthaltende praeparationen"
DE3121676 1981-06-01

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US06381837 Continuation 1982-05-25

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US (1) US4536509A (de)
EP (2) EP0068144B1 (de)
JP (1) JPS57203070A (de)
AT (1) ATE16282T1 (de)
AU (1) AU562814B2 (de)
BR (1) BR8203194A (de)
CA (1) CA1182120A (de)
DD (1) DD202704A5 (de)
DE (2) DE3121676A1 (de)
DK (1) DK244382A (de)
ES (1) ES8303364A1 (de)
GR (1) GR76818B (de)
HU (1) HU188577B (de)
IL (1) IL65924A (de)
MY (1) MY8700827A (de)
NZ (1) NZ200791A (de)
PH (1) PH18564A (de)
PT (1) PT74981B (de)
RO (1) RO85325B (de)
SU (1) SU1175347A3 (de)
TR (1) TR21327A (de)
ZA (1) ZA823770B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990009273A1 (en) * 1989-02-16 1990-08-23 Wm. Wrigley Jr. Company Food packaging improvements

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3406908A1 (de) * 1984-02-25 1985-09-05 Hoechst Ag, 6230 Frankfurt Neue triazolylalkylderivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenbehandlungsmittel
DE3579347D1 (de) * 1984-04-05 1990-10-04 Ici Plc Azolylpropanole.
ATE46150T1 (de) * 1984-05-23 1989-09-15 Ciba Geigy Ag Mikrobizide 1-fluor-1-azolyl-2,2diarylethanderivate.
EP0194064A3 (de) * 1985-03-06 1988-11-17 Imperial Chemical Industries Plc Aralkyl-substituierte Azolderivate
DE3508909A1 (de) * 1985-03-13 1986-09-18 Bayer Ag, 5090 Leverkusen Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole
US4729986A (en) * 1986-04-24 1988-03-08 E. I. Du Pont De Nemours And Company Fungicidal triazoles and imidazoles
EP0276583A1 (de) * 1987-01-29 1988-08-03 Instituto de Investigacion Y Desarrollo Quimico Biologico S.A. Imidazol-Derivate, Verfahren zu ihrer Herstellung und ihre fungizide Eigenschaften
EP0458160A3 (en) * 1990-05-25 1992-03-18 Sociedad Espanola De Especialidades Farmaco-Terapeuticas, S.A. Substituted diphenylmethane derivatives as analgesic or anti-inflammatory agents
US6593436B2 (en) 2000-11-29 2003-07-15 Crompton Corporation Continuous manufacture of silicone copolymers via static mixing plug flow reactors

Citations (4)

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Publication number Priority date Publication date Assignee Title
US4115578A (en) * 1975-12-18 1978-09-19 Rohm And Haas Company 1-Substituted aralkyl imidazoles
BE867245A (fr) * 1977-05-19 1978-11-20 Rohm & Haas 1,2,4-triazoles substitues et leurs derives utilisables comme fongicides, et procedes pour leur preparation.
US4275071A (en) * 1978-07-26 1981-06-23 Recordati S.A. Imidazole derivatives
EP0037049A1 (de) * 1980-04-02 1981-10-07 Bayer Ag Biphenylyl-imidazolylethan-Derivate, Verfahren zu ihrer Herstellung und diese Verbindingungen enthaltende Arzneimittel

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FR1487326A (fr) * 1966-01-18 1967-07-07 Clin Byla Ets Dérivés imidazoliques et leur préparation
SE7600674L (sv) * 1975-02-05 1976-08-06 Rohm & Haas Fungicider
AT377515B (de) * 1977-10-19 1985-03-25 Wellcome Found Verfahren zum herstellen von neuen 1-arylalkyl-imidazolderivaten und deren salzen
DE2851059A1 (de) * 1978-11-25 1980-06-04 Bayer Ag 1-(biphenylyl-propyl)-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2912288A1 (de) * 1979-03-28 1980-10-09 Bayer Ag Verfahren zur herstellung von hydroxyethyl-azolen
DE2935452A1 (de) * 1979-09-01 1981-03-19 Basf Ag, 6700 Ludwigshafen N-phenylpropylsubstituierte azole, verfahren zu ihrer herstellung und diese enthaltende fungizide

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US4115578A (en) * 1975-12-18 1978-09-19 Rohm And Haas Company 1-Substituted aralkyl imidazoles
BE867245A (fr) * 1977-05-19 1978-11-20 Rohm & Haas 1,2,4-triazoles substitues et leurs derives utilisables comme fongicides, et procedes pour leur preparation.
US4275071A (en) * 1978-07-26 1981-06-23 Recordati S.A. Imidazole derivatives
EP0037049A1 (de) * 1980-04-02 1981-10-07 Bayer Ag Biphenylyl-imidazolylethan-Derivate, Verfahren zu ihrer Herstellung und diese Verbindingungen enthaltende Arzneimittel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990009273A1 (en) * 1989-02-16 1990-08-23 Wm. Wrigley Jr. Company Food packaging improvements

Also Published As

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EP0068144A1 (de) 1983-01-05
IL65924A0 (en) 1982-08-31
EP0068144B1 (de) 1985-10-30
PT74981A (en) 1982-06-01
RO85325B (ro) 1984-10-30
EP0146064A3 (de) 1986-12-30
PT74981B (en) 1984-12-10
GR76818B (de) 1984-09-04
TR21327A (tr) 1984-03-01
ATE16282T1 (de) 1985-11-15
PH18564A (en) 1985-08-09
ZA823770B (en) 1983-03-30
DE3121676A1 (de) 1982-12-16
DD202704A5 (de) 1983-09-28
RO85325A (ro) 1984-09-29
AU8433082A (en) 1982-12-09
HU188577B (en) 1986-04-28
JPS57203070A (en) 1982-12-13
SU1175347A3 (ru) 1985-08-23
CA1182120A (en) 1985-02-05
DE3267123D1 (en) 1985-12-05
BR8203194A (pt) 1983-05-17
MY8700827A (en) 1987-12-31
IL65924A (en) 1987-02-27
AU562814B2 (en) 1987-06-18
ES512531A0 (es) 1983-02-16
NZ200791A (en) 1985-10-11
EP0146064A2 (de) 1985-06-26
ES8303364A1 (es) 1983-02-16
DK244382A (da) 1982-12-02

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